Water → HCID 22466150, compound

HRID 1934310Notes

Reaction equation

HRID 1934310 reaction equation
BrBr.[NH2:3][C:4]1[CH:5]=[C:6]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=2)[C:7]([F:11])=[CH:8][C:9]=1[Cl:10].[S-:23][C:24]#[N:25].[Na+].O>C(O)(=O)C>[NH2:25][C:24]1[S:23][C:5]2[C:6]([C:12]3[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=3)=[C:7]([F:11])[CH:8]=[C:9]([Cl:10])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516871Sodium thiocyanateHCID 11131164HCID 11131164, compound

Product 1

HCID 22466150HCID 22466150, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

At about 20° C., a solution of 37 g (234 mmol) of bromine in 10 ml of glacial acetic acid was added over a period of 10 minutes to a solution of 38 g (117 mmol) of 2-(3-amino-4-chloro-6-fluorophenyl)-3-chloro-5-trifluoromethylpyridine and 38 g (468 mmol) of sodium thiocyanate in 500 ml of glacial acetic acid. The reaction mixture was subsequently stirred at room temperature for 10 hours and then poured into 2 l of water. The product was then extracted with 3×500 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate and (finally concentrated. The crude product was purified by silica gel chromatography (eluent: cyclohexane/ethyl acetate =4:1→1:1). Yield: 13%; m.p.: 230-235° C.

Workup

  1. extractionThe product was then extracted with 3×500 ml of ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentration(finally concentrated
  4. customThe crude product was purified by silica gel chromatography (eluent: cyclohexane/ethyl acetate =4:1→1:1)

Sources & evidence

ORD record
ord-d716e8d73146420fa34b719602ca5048
Source dataset
uspto-grants-2002_05
Patent number
US06383986B1

Reaction notes

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